Good Luck Teddy
by Sellybelly411
Summary: Teddy Duncan heads to New York City in hopes of re-connecting with her ex-girlfriend, Jessie Prescott. But she is devastated when she learns that Jessie has forgotten all about her.
1. Forgotten

Sitting in the park brought back many old memories, ones I hoped could be re-created. The spot where I was sitting was the last place me and Jessie Prescott had talked. The same spot where she had broken up with me. That memory I didn't want to re-live.

" _You said you loved me!" I had said in that one heart wrenching day._

" _And I do, Teddy. In do. It's just, this is such a big opportunity for me."_

" _Fine." I said angrily, grabbing my purse and standing up._

" _Teddy…" She reached out to me, but I was already gone._

When I had heard she was going to be making a visit to New York, I sprung for the chance. I checked the time; 9:30. She should be arriving in the park sooner or later. I had seen a news report yesterday that Jessie was coming to do a photo shoot.

But clearly, _I_ wasn't the only one who heard the news. The park was crowded with teenage girls. When they began to scream, I knew she must be here. A security guard ushered Jessie through the crowd, who was smiling and waving at the adorning crowd.

"Jessie!" I called, once she was close enough to me. Her dark red locks bounced as she turned her head around. I waved at her, and she tilted her head. Finally, she smiled and walked over to me. I was bouncing with anticipation, "Jessie!"

I pulled her into a hug, inhaling the scent of peaches from her red locks, "It's so great to see you again."

And when I pulled away, I saw nothing on her eyes. Jessie tucked away stand or her hair behind her left ear, "… Okay?"

"What's wrong? I thought you'd be happier to see me." I said, "But your kind of acting like you don't remember me at all."

She crossed her arms, "Should I know you?"

My heart broke in half, "You, you must be joking Jessie, its me. Its Teddy Duncan."

"Did I take a photo with you someday?"

I started to cry, "No. Oh my God, this can't be happening. I didn't take any photos with you, or bump into you somewhere, or go to one of your stupid events." I said, counting off on my fingers.

"First of all, they're not stupid. Second, if you never did all that stuff than why do you insist that we know each other?"

"Beca-Because Jessie, I'm your ex-girlfriend."

"Um, no. That's impossible, I would never date a girl."

"Um, yes you would." I imitated, "C'mon, we dated for three years! You only broke up with me because of your stupid movie career."

Jessie looked at me like I was insane.

"I flew all the way to New York just to see you."

"So? A lot of fans do that."

"I-I'm not a fan, Jessie! I didn't fly here to be some crazy fangirl. I came here to ask you to be my girlfriend again!" I shouted.

"Well, you must be delusional, because I don't date girls." She said, patting my shoulder before walking away.

 _I can't believe this._

"Don't take it personally, Teddy."

I jumped on surprise. I hadn't even noticed that Emma Ross had taken a seat beside me.

"But…"

The blonde teenager smiled at me, "I know. Jessie's just not the same since she went off to Hollywood." She explained.

"She didn't forget _you_ though, did she?" I asked.

"I don't know, but I wouldn't put it past her. She's coming over tonight for dinner to talk about her next movie. You want to come eat with us?"

I smiled, "Sure. I really don't have any other place I need to be. "

At eight- 'O-clock that night, I arrived in the Ross house wearing a light blue dress. I heard chartering from the kitchen, and nervously walked in. Jessie was talking to Martin and Christina Ross about the movie deal. The kids weren't in the room yet, so I backed out.

"Teddy!" A little girl voice shouted. Her loud voice made heads turn. The redhead seemed curious and a little frightened to see me there. Zuri Ross jumped onto my back, and I carried her into the kitchen. After I sat her down on her chair, the other Ross kids ran on and gave me hugs.

"What are you doing here?" Jessie asked.

I cleared my throat, "Um… Emma invited me. "

She raised her eyebrow, "Did she?"

Emma moved closer to me, "I did."

The redheaded celebrity walked closer to me. She seemed skeptical, as if she didn't believe I was telling the truth.

"Jessie." I said, offering a kind smile.

"Yeah?"

"I can't always leave, if you want."

"Why would you? Oh my Gosh, are you two breaking up again?" Zuri asked.

I blushed, "Sweetie, we never got back together. Jessie doesn't remember a thing about me. "

The girl looked at her former Nanny, "Really? Nothin'?"

"No. Should I?"

" _Yes!"_ All the Ross kids shouted.

Jessie stared at the kids in awe. They seemed offended that she didn't remember me. But not as upset as I was.

"Maybe this wasn't such an innovative idea after all."

The kids frowned at the sight of me. Tears were dripping down my face like an endless waterfall. I walked away, my boots echoing against the tile floor. But then I paused and opened my wallet. I took a poloried out of the plastic pocket and offered it to her, "Here. Keep it."

The photograph was the two of us on our second to last date. We were standing on top of a table holding milkshakes. She had her left arm around my waist and was kissing me on the cheek. I had my right arm up in the air, as if I was making a toast. With my left hand, I held my index finger against my lips as if I was telling someone to keep quiet.

We had been so in love back then. Or maybe it was just me, maybe I was the fool who thought a girl like her could be in love with me. Jessie had told me multiple times how much she loved me. But if that was true, she wouldn't have forgotten me.

Had I been nothing to her all along?

I turned my back to her before she could say anything. I doubted she wanted to, because she was too freaked out by the photograph to form any words. Someone yanked on the end of my shirt and I turned around. Zuri was standing there holding her arms wide. I smiled at her through my tears and gave her a hug.

"I'm sorry, Teddy." She said, "I know its not the same, but if it makes any difference I love you." She squeezed me tighter.

"I love you too, Zuri."

I waved goodbye to the kids and exited the apartment, trying to hide my tears that just wouldn't stop.


	2. Have it All

Have it All

Okay, they say nobody can have it all. But clearly, that didn't apply to Jessie. Because she _did_ have it all. She had her money, her career, her celebrity friends, and everybody's adoration. And to her, I was just another fan. Nothing worth paying attention to.

The fact that I knew that made me cry harder. I was sitting in the park again just thinking of what I should do next.

Back in the Ross house, Jessie was trying you figure out what was going on. She just couldn't stop staring at the photo I have given her.

"How…?" Jessie asked.

"We told you, Jessie. You and Teddy used to date." Emma said, taking the picture from her. The redhead still seemed not entirely convinced. But still, she turned to the girl, "Tell me more."

The kids smiled and started to tell the story, Jessie hanging onto every word they said.

I was at the bus station now when this was happening. I needed a ride back to the airport. She didn't remember me, so what's the point? I might as well just go home to my apartment in Connecticut where I belonged. I held my buss pass tightly in my hand and tucked it in my pocket. It was awfully windy, so I pulled my hair back into a ponytail and zipped up my jacket.

I heard a loud whoosh and an engine putter. My bus was here. I got up off my seat and handed the driver my ticket. I took a seat on the left side and gazed longingly out the window. Would she come for me? Probably not.

It was just as we turned a corner when I saw the Ross children, along with Jessie waving desperately at me. I wanted to get off, but it was too late. The bus rode on and on, until it stopped at my destination. I sighed and handed the driver a tip and walked through the bustling crowd to the airport.

I purchased a ticket to Connecticut and smiled at the desk lady. My flight left in no less than an hour. I didn't have all that much time, so I grabbed some lunch from the food court and a latte from Starbucks. About the time I finished my flight was called. I was headed home.

Back at the train station, Emma and Zuri were glaring daggers at Jessie, who looked uncomfortable.

"This is your fault." Emma said, crossing her arms.

" _Mine?"_ Jessie scoffed, "How is this my fault?"

"Um, hello! For forgetting Teddy! If you had just believed us, then she wouldn't be heading back home now!"

"Well, its not my fault that I don't remember the girl. She must have not been very important to me. If she was, I wouldn't have forgotten her!"

"This is absolutely your fault, Jessie! You mean everything to her. I hate saying this, but ever since you became a celebrity you've been acting like a total snob."

Jessie gasped, "I have _not!"_

"Yes, you have." Zuri said, crossing her arms.

"It's a miracle you even remember us." Emma said.

"Of course I remember you guys! Why wouldn't I? You meant so much to me!"

"What I think—" Ravi said, "is that because we are the children of a director, that is why you remember us."

The rest of the kids nodded in agreement.

"And since Teddy isn't famous, you've forgotten all about her. You broke her heart, Jessie." Emma said.

The kids walked away from her, each with the same exact look of disappointment on their faces. Jessie just stood there, all alone, aghast.

I sat in my seat listening to music on my phone. The airplane was about to take off, but I didn't care all that much. I was going home. I was going to lay in my bed for three weeks or more, crying my eyes out. Like I did when I found out my ex-boyfriend from high school was cheating on me.

"What am I supposed to do?" Jessie asked to herself.

"How about smile for the camera?" A voice said behind her, and she was surrounded by cameras.

Jessie groaned and covered her eyes, shoving through the crowd to check the bus schedule. The next bus going to the airport would be here in twenty minutes. She took out her phone and dialed Emma's number.

" _Hello?"_

"Hi, Emma. Its Jessie."

" _I know its you, because your name is in my contact list."_

She ignored the comment, "The point is, I need you to tell me where Teddy lives."

" _Why? Finally remember her?"_

"No, but I feel like I need to make it up to her. So, do you know where she lives or not?"

" _Fine…she lives in Connecticut now."_

"Now? Where did Teddy _used_ to live?"

" _Colorado. She moved because she got accepted to Yale."_

"Yale? Wow, that's one prestigious collage. Wait, how do you know all this?"

" _Unlike you,_ I _keep in touch with her. But unluckily for you, I don't know_ where _she is. Address wise, I mean. As far as I know she lives in an apartment."_

"Thanks Emma." Jessie ended the call.

She purchased a bus pass and soon was on her way to Connecticut. This was bad. This was very, very bad.

It was now she knew that Emma was right, her career had taken a toll on her. She had never meant to hurt anyone's feelings. She never meant to forget anybody. It just…happened. And it was all her own fault.

 _Stupid, stupid Jessie._ I thought to myself.

I was mad and sad at the same time. I had been crying so hard that the neighbors upstairs heard me. I should hate Jessie, I really should. But somehow in my broken heart, I still loved her.

I was a mess. I was a pathetic mess. I had never felt this way about anybody in my entire life. I wished my best friend Ivy was here, because she would know how to console me. I knew I would never see my ex-girlfriend again.

But then the door opened.


	3. Broken

Broken

I nearly choked on my water at the sight of Jessie. She was here, in my room. What was she doing here?

"Teddy…" She said smoothly.

I turned away, so I wouldn't have to see her.

"What are you doing here?" I blubbered, hugging my box of tissues.

"I came to say I'm sorry." Jessie said, "I'm sorry for forgetting you."

"You remember?" I asked in a squeaky whisper.

"No."

I pulled myself up, legs dangling over the side of the bed. She was staring at me.

"Seriously? You come all this way to say, 'I'm sorry' and yet you still have no memory of me? I was right all along, you don't love me. You never have."

"Teddy." She said quietly, "You're being ridiculous."

"Yeah, I am. Because I can't do this anymore. I can't keep trying. You were everything to me, and then you go off to Hollywood."

"It's not—"

"Oh, it's not stupid? Is that what you were going to say? Because I think otherwise. I thought we'd be together forever. Then, you took me on a date in the park. You told me you had this opportunity you just couldn't resist. You chose your career over me, Jessie."

She was staring at me now.

"And the worst part is, no matter how much you've hurt me, I still love you." I said.

She didn't say anything to me.

"Just get out, Jessie. Just go." I ordered, pointing at the door.

"Teddy, please."

"I said, get out."

I crashed down onto my pillow and sobbed some more. I heard the echo of her heels walk away, then stopped. I looked up once and saw she was gone. Much like shattered glass; I was broken. My heart felt like it had been smashed by a mallet.

I sniffled and shut my eyes, drifting back to sleep. She had finally left for good.

What I didn't know, was that she was still outside. And once I had fallen asleep, she came back in.

My alarm on my phone rang, and I quickly got dressed and did my makeup. I shoved a packet of tissues into my purse and ran out the door. I worked as a volunteer at a Children's Medical Center and didn't want to be late.

I locked the door behind me. I didn't even notice Jessie staring at me as I ran out the door. She was asleep on my couch and apparently very determined to earn my forgiveness. She just didn't know how.

I walked through the self-opening doors and grabbed my Volunteer pass off the information desk.

"Where does he need me today?" I asked the woman who worked behind the desk.

"Level Three, room 204A." She responded.

I nodded and waved goodbye, heading upstairs. I entered the hospital room and smiled at the doctor, who was consoling a crying child. He held a syringe in one of his gloved hands.

"Ah, Teddy!" He said, turning to me.

I didn't respond but headed over to the girl's side instead. She was wearing a pink hospital gown and was holding a fuzzy bear close to her chest.

"Hi, sweetie." I said, smiling at her.

"Are you going to poke a needle in me?"

"No." I said softly, "What's your name?"

"Sophie." She answered in a timid voice.

"Nice to meet you Sophie, I'm Teddy."

She giggled, "Teddy? Like in Teddy Bear?"

I nodded and smiled as she continued to laugh.

"What are you so scared of?" I asked her.

"He's got a big, pointy needle." She pointed at the doctor.

I nodded, "He does. But you have no reason to be scared, Sophie. Because guess what?"

"What?"

"Getting a shot makes you a big, strong girl. Like…like Wonder Woman."

"I'll get super powers?" She said excitedly.

"Sort of. You'll get the power to be brave, and you'll be able to battle any problems that come your way." I explained, "Don't you want to be brave?"

She nodded.

"Great. So what do you say, will you let him give you your shot?"

"Okay!" Sophie answered, offering the doctor her arm, "Will you hold my hand?"

I nodded and took her other hand, talking to her while the doctor gave her her shot. When it was over, I gave her a big hug, "See? What did I tell you?"

She smiled and hugged me close. Sophie picked up her bear and handed it to me, "For you."

"I can't take that. He belongs to you!"

"It's a girl, and her name is Rosie." She explained, "And she wants to be with you."

"Are you sure?"

"Mm-hm." She answered, practically forcing the bear into my hands.

I smiled at her and left with the bear in my arms. Ever since my little sister Charlie was born, I've had a knack for taking care of little kids. Thinking of her inspired me to do a new video diary. I went into the hallway and pulled out my cam corder, flipping the screen to it would face me.

"Hi, Charlie. It's your big sister Teddy here, and I wasn't planning to do a video diary today. In fact, I haven't made one of these for you since I left for Yale. But anyway, I'm a volunteer now at a children's hospital. And this little girl gave me her bear!" I lifted the bear so it could be captured in-frame.

"What are you doing?" A man's voice said from around the corner. I flipped my camera's lens the other way and pointed it at a young doctor, who was shouting at none other than Jessie Prescott.

"I was just trying to find the bathroom!"

"It's by the registry desk, not in our medical rooms. Besides, only medal staff and volunteers can be in here."

"I…would like to disagree with that fact." She said, "Patients are allowed as well."

"Yes, patients are allowed. But I thought that was implied."

"Well, you thought wrong!" She shouted back.

They started shouting over each other until push came to shove (literally) both Jessie and the Doctor were covered in saline. I came out of my spot and pointed my camera right at them. I leaned in-frame and motioned at the two of them, who were on the ground looking miserable.

The doctor looked up at me, then at the girl, "Teddy?"

"Yeah, Dr. Wheeler?" I pointed the camera at him.

"You know this girl?" He pointed to the wet-headed redhead beside him.

I thought about it for a moment, "No. No I don't."

Jessie eyes me, "Seriously? Now is the time you say you don't know me?"

"I'm sorry, have we met before…?"

She flipped her hair, causing some saline to splash onto the doctor's face. She looked up to him, her mouth shaped into a perfect 'O'. Behind the camera, I tried to hide a laugh. I leaned in-frame again.

"Yeah, I don't think Jessie will be coming back here anytime soon. So, in the meantime, she'll need some good luck, Charlie." I shut the camera closed and helped Jessie up, then the doctor.

He bid me goodbye, then shot one angry glare at Jessie. I bent over laughing, ignoring the stink eye I was getting from Jessie. She grabbed my camera out of my hands, "You are deleting this."

I shook my head, "No way. That was gold." I grabbed the camera back and zipped it back into my bag, continuing to laugh.

"You are _evil."_

Jessie walked along behind me, very, very slowly. I didn't stop laughing until we reached the parking lot.

In fact, I was so amused that I didn't even wonder why she was here. That was, until we got into Ed (my car).

"Why are you here?" I asked seriously, "I thought you left last night."

"I was planning to, yes. But then I had a better idea."

"Like?" I asked, turning on the engine.

"Teddy, would you like to go on a date with me?"

I tried to suppress a scream of joy. Instead, I looked at her, my mouth hanging open.

 _"Excuse me?"_ I asked.

"A date. You and me."

"I thought you didn't date girls."

Jessie brushed me off, "Oh, please. I only tell people that, so the reporters will get off my back. If anyone found out I was a lesbian, my career would be over."

 _This can't seriously be happening._

"So, for our date. I was thinking some place dark, and in a secluded area." She said, "What do you think?"

"No." I said, making her shut up.

"Excuse me?"

"I said no. I don't want to be someone's sympathy date. _Especially_ when you are humiliated to be around me." I explained.

"Oh, come on Teddy." She placed her hand on my arm, but I shook it off.

"Please? I promise I'm not doing this to make you feel better."

"Okay, let's say you are actually into me. Why do we have to be in a secluded area? Why can't we be in front of other people?"

"Because."

"Because? Because what?"

"Because, um…"

"I knew it. You don't want to be seen with me in public."

"You're being ridiculous." She said.

"Really? Then would you like to go have lunch with me tomorrow, Jessie?"

"No. I have a meeting with my producers that day."

I shook my head, every part of my body furious at Jessie. She was talking, but I turned my ears off. I hated that I didn't hate that girl.

And I hated myself for loving her.


	4. There For You

There for You

After yesterday's hospital fiasco, I let Jessie spend one night at my apartment. All her things were in my bedroom, and she hadn't purchased a plane ticket yet.

I parked my car in front of the airport and unlocked all the car doors. I heard her buckle click and she got out of the car with her bag. She was almost to the self-opening doors when she thought better of it and ran back over to me.

"What are you doing?" I asked, as she forced me out of my car.

She reached over and hugged me close to her chest. So close in fact, that I could hear her heart beating.

 _Ba-Bump, Ba-Bump._

It was a rather steady beat. She cupped my face with her hands and looked into my plain brown eyes. Her hazel eyes sparkling with interest as she observed me. I stared at her oddly. What did she think she was doing?

A warmness spread across my cheek when her lips pecked it. My mouth suddenly felt dry, and as I looked up at her I saw she was very entertained by all this. She hugged me quickly and waved goodbye, tugging her luggage behind her.

Suddenly, I didn't want her to go.

I dialed my best friend Ivy's number and told her everything. She was outraged throughout the whole story. At least, until the end which dialed her down to just furious.

"Teddy, do you want me to come up there?" She asked.

"But aren't you supposed to spend the weekend with your parents?"

There was a long pause before she finally answered, "Yeah. I'm comin' up there."

I laughed and hung up.

At home now, I took off my sneakers and turned on the radio. And by radio, I mean Pandora. My phone blasted music from the sixties to now. I snapped along to the music.

The music was interrupted by the ringing of my phone. As guilty as I admit it, it was one of her songs. I picked it up and didn't bother to check the caller ID.

"Hello?"

"Teddy, its me!" Came the terrified voice of Jessie, "I need you. Now."

"Why? What happened?"

"I don't know. But I suddenly woke up in an expensive fresh restaurant in downtown Connecticut." She said.

"A-alright, I'll head over." I said, already grabbing my coat.

"Wait! Make sure to wear something fancy, when I woke up I saw kids getting kicked out because they were wearing what the host called 'casual wear.'"

"Okay, Okay. Just let me get dressed. Wait, do you happen to know what restaurant you're at?"

" _Le Petit Café."_

"Okay." Then I hung up.

I got my dress on very quickly, but it was the shoes I had trouble with. It took a good ten minutes for me to shove those on my feet. Then I was on my way.

I walked through the circling door holding a silver clutch. I greeted the host with a smile and asked him if he knew where Jessie was being held hostage. He just looked at me funny and pointed at a table with a candelabra sitting atop, with rose petals scattered about the table. My jaw dropped when I saw her. She was sitting in the right seat wearing sparkly red dress with a black feathered skirt. She waved at me, and I stomped over to her.

"What is this?" I asked.

"Our first date."

"Oh, really? And here I thought you didn't go on dates with girls in public?"

"You're worth it." She said, pulling my chair out for me.

"You tricked me."

"I knew you would've said no if I'd asked directly."

I didn't say anything back to her. I always had that problem with Jessie. I never knew what to say or do when I was around her.

"You look beautiful." She smiled.

I looked down at my elegant sapphire blue, off the shoulder mermaid tail dress. It was beautiful, I did admit. But I didn't even look half as good as Jessie did right now, which I told her.

"Be quiet." She commanded, "If anything, you look better than me."

I rolled my eyes and continued to say nothing to her.

The waitress came by bearing us fancy French baguettes. I thanked her timidly and tore a small piece off the end and dipped it into the butter.

"Come on, Teddy." Jessie begged ten minutes later, "You have to say something to me."

I shook my head and she frowned.

"Look, I'm sorry for tricking you. I know you're mad and all—"

"That's not it." I admitted, looking up at her.

"What do you mean?"

"I'm not mad, not really." I lifted my head up, "I just don't know what to talk to you about. My life isn't the most interesting story to tell."

"I'm not asking for your life story, Teddy. I just want to actually talk to you." She reached out and held my hand, "Tell me something about yourself."

"O-Kay…" I trailed off, "Well, I have for siblings."

It was a dumb thing to say, but it was the first thing that popped into my head. I wasn't even sure if it was all that interesting.

She looked taken aback.

"Five kids? I can't imagine the stress of tha—" She paused, "I—I mean, that is interesting."

I rolled my eyes and looked away from her.

"I'm sorry, Teddy. I'm not very good at this."

"What? Hanging with the middle class?"

"No. Dating. Its like my love life is cursed or something, because I am always the one to ruin a relationship." Jessie sighed, "Look, I know I messed this up. I shouldn't have tricked you, Teddy. And I'm sorry, if you aren't having a good time I wouldn't blame you if you left."

I rolled my eyes, "Jessie, shut up."

She looked at me, "Excuse me?"

"You are being way overdramatic. I'm having an amazing time, even though you had to trick me into it."

"Aww, Teddy. I'm so glad!" She leaned over the table and pecked me on the cheek. Camera flashes went off outside the restaurant window.

"Oh, Shit." Jessie swore under her breath.

I looked over her shoulder and noticed the endless crowd of paparazzi.

"I can't let them see me here with you."

I stood up, _"Excuse me?"_

She waved her hands at me, just realizing the words that had come out of her mouth. I slammed my napkin onto the table and walked past her. But then a sly smile spread across her face as I saw her standing by the table looking guilty.

I walked over to her and dipped her like in the _V-J Day in Times Square_ photo, kissing her on the mouth before she could protest. Cameras flashed like dancing Christmas lights. I walked out of the restaurant amused, leaving a shell-shocked Jessie in the dust.

Revenge was sweet. Literally, Jessie's strawberry lip gloss had rubbed off on me.


End file.
